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Omeprazole

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Name

Omeprazole

EINECS 201-212-8
CAS No. 73590-58-6 Density 1.371 g/cm3
PSA 96.31000 LogP 3.76540
Solubility Easily soluble in dichloromethane, chloroform and methanol Melting Point 156 °C
Formula C17H19N3O3S Boiling Point 599.991 °C at 760 mmHg
Molecular Weight 345.422 Flash Point 316.663 °C
Transport Information N/A Appearance white crystalline solid
Safety 26-36-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 73590-58-6 (Omeprazole) Hazard Symbols IrritantXi
Synonyms

Pepticus;Zoltum;Lensor;Pepticum;Indurgan;1H-Benzimidazole,5-methoxy-2-[[(4-methoxy- 3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-;Prilosec (TN);Omerprazole;Omisec;Gibancer;Prazidec;Ulzol;Omezolan;Ulsen;Ortanol;Victrix;Omeprazon;Omapren;Zimor;Procelac;Dudencer;5-Methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridyl)methyl)sulfinyl)benzimidazole;Proclor;Antra;Omesek;Omeprol;Mopral;Gasec;Peptilcer;Nopramin;Tedec Ulceral;Omid;Zegerid;Result;Ulcesep;Gastroloc;Losec;Ompanyt;2-(((3,5-Dimethyl-4-methoxy-2-pyridyl)methyl)sulfinyl)-5-methoxy-1H-benzimidazole;Omed;Prilosec OTC;Antra MUPS;Omeprazolum [INN-Latin];Omebeta 20;Omizac;Zepral;Demeprazol;Ozoken;Omegast;Zefxon;Omeprazol [INN-Spanish];Danlox;Ceprandal;Olexin;Belmazol;Ulcometion;Erbolin;Miracid;Osiren;Prazolit;Ulcozol;Inhipump;Nilsec;Exter;Regulacid;

Article Data 76

Omeprazole Synthetic route

86604-75-3

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride

37052-78-1

6-methoxy-1H-benzoimidazole-2-thiol

73590-58-6

omeprazole

Conditions
ConditionsYield
Stage #1: 6-methoxy-1H-benzoimidazole-2-thiol With sodium hydroxide In ethanol; water at 70 - 90℃;
Stage #2: 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride With hydrogenchloride In ethanol; water at -10 - 30℃; for 4h; Reflux;
96%
73590-85-9

omeprazole sulfide

73590-58-6

omeprazole

Conditions
ConditionsYield
With dihydrogen peroxide; molybdenyl acetylacetonate In methanol; water at 0 - 5℃; for 3h;91%
With dihydrogen peroxide; sodium carbonate; sodium tungstate In methanol; water at 20℃; for 0.666667h; Product distribution / selectivity;91%
With sodium hydroxide; dihydrogen peroxide; sodium tungstate In methanol; water at 20℃; for 0.666667h; Product distribution / selectivity;88%
1080503-61-2

(-)-menthyl 5-methoxy-2-benzimidazolylsulphinate

109371-19-9

2,3,5-trimethyl-4-methoxypyridine

73590-58-6

omeprazole

Conditions
ConditionsYield
Stage #1: 4-methoxy-2,3,5-trimethylpyridine With n-butyllithium In tetrahydrofuran at -90 - -80℃; for 0.5h;
Stage #2: (-)-menthyl 5-methoxy-2-benzimidazolylsulphinate In tetrahydrofuran at -80 - -20℃;
Stage #3: With water In tetrahydrofuran at -20℃;
86%
85-44-9

phthalic anhydride

5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridinyl)methylthio]-1H-benzimidazole hydrochloride

73590-58-6

omeprazole

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide; sodium carbonate In water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran85.9%
73590-85-9

omeprazole sulfide

A

73590-58-6

omeprazole

B

omeprazole sulphone

Conditions
ConditionsYield
With oxone; sodium hydrogencarbonate; bis(acetylacetonate)oxovanadium In methanol; water at -2 - 0℃; for 5.5h;A 84%
B n/a
With oxone; sodium hydrogencarbonate In methanol; water at 0℃; for 5.5h;A 84%
B 0.15%
With oxone; sodium hydrogencarbonate In methanol; tetrabutylammomium bromide; water at -2 - 3℃; for 7.5h; Product distribution / selectivity;A 84%
B n/a
aqueous sodium metabisulphate

aqueous sodium metabisulphate

(acac)2

(acac)2

aqueous tert-butyl hydroperoxide (TBHP)

aqueous tert-butyl hydroperoxide (TBHP)

73590-85-9

omeprazole sulfide

73590-58-6

omeprazole

Conditions
ConditionsYield
In ethanol79%

C10H12N2O3S

84006-10-0

(chloromethyl)-4-methoxy-3,5-dimethylpyridine

A

C18H24N2O2

B

73590-58-6

omeprazole

Conditions
ConditionsYield
Stage #1: (chloromethyl)-4-methoxy-3,5-dimethylpyridine With [Mg(anthracene)(THF)3] In tetrahydrofuran at -5 - 0℃; Inert atmosphere;
Stage #2: C10H12N2O3S In tetrahydrofuran at -5 - 30℃; for 4h; Inert atmosphere;
A n/a
B 30%
73590-85-9

omeprazole sulfide

A

73590-58-6

omeprazole

B

8-methoxy-2,4-dimethyl-5-thioxo-5-hydro-pyrido<1',2':3,4>imidazo<1,2-a>benzimidazol-3-one

C

omeprazole sulphone

Conditions
ConditionsYield
With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate In ethanol; acetate buffer at -5℃; pH=5.0; Oxidation; cyclization;
142885-92-5

5-methoxy-2-[[(4-methoxy-3,5-dimethylpyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzimidazole

73590-58-6

omeprazole

Conditions
ConditionsYield
With iodobenzene; silver(I) acetate; Ru(III)(N,N'-bis(salicylidene)-o-phenylenediamine)(triphenylphosphine)Cl In dichloromethane Heating / reflux;
With iodobenzene; silver(I) acetate; Ru(III)(salen)(PPh3)Cl In dichloromethane Heating / reflux;
aqueous sodium metabisulphite

aqueous sodium metabisulphite

73590-85-9

omeprazole sulfide

73590-58-6

omeprazole

Conditions
ConditionsYield
With tert.-butylhydroperoxide; VO(acac)2 In toluene

Omeprazole Specification

The Omeprazole, with the CAS registry number 73590-58-6, is also known as 2-(((3,5-Dimethyl-4-methoxy-2-pyridyl)methyl)sulfinyl)-5-methoxy-1H-benzimidazole. It belongs to the product categories of Drug bulk; Active Pharmaceutical Ingredients; Omeprazole; Intermediates & Fine Chemicals; Pharmaceuticals; API's; ATPase. Its EINECS number is 200-636-0. This chemical's molecular formula is C17H19N3O3S and molecular weight is 345.42. What's more, its systematic name is 6-Methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl}-1H-benzimidazole. Its classification codes are: (1)Anti-ulcer agents; (2)Depressant [gastric acid secretory]; (3)Drug / Therapeutic Agent; (4)Enzyme inhibitors; (5)Gastrointestinal Agents; (6)Human Data; (7)Mutation data; (8)Reproductive Effect. This chemical is a proton pump inhibitor used in the treatment of dyspepsia, peptic ulcer disease (PUD), gastroesophageal reflux disease (GORD/GERD), laryngopharyngeal reflux (LPR) and Zollinger–Ellison syndrome. Omeprazole is one of the most widely prescribed drugs internationally and is available over the counter in some countries. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides.

Physical properties of Omeprazole are: (1)ACD/LogP: 2.452; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.39; (4)ACD/LogD (pH 7.4): 2.44; (5)ACD/BCF (pH 5.5): 37.10; (6)ACD/BCF (pH 7.4): 41.57; (7)ACD/KOC (pH 5.5): 443.46; (8)ACD/KOC (pH 7.4): 496.87; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 96.31 Å2; (13)Index of Refraction: 1.669; (14)Molar Refractivity: 94.021 cm3; (15)Molar Volume: 251.869 cm3; (16)Polarizability: 37.273×10-24cm3; (17)Surface Tension: 75.2 dyne/cm; (18)Density: 1.371 g/cm3; (19)Flash Point: 316.663 °C; (20)Enthalpy of Vaporization: 89.315 kJ/mol; (21)Boiling Point: 599.991 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

Mechanism of action of Omeprazole: it is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton pump, omeprazole blocks the final step in acid production, thus reducing gastric acidity.

Pharmacokinetics of Omeprazole: The absorption of omeprazole takes place in the small intestine and is usually completed within 3–6 hours. The systemic bioavailability of omeprazole after repeated dose is about 60%. Omeprazole bioavailability is significantly impaired by the presence of food and, therefore, patients should be advised to take omeprazole with a glass of water on an empty stomach (i.e., fast for at least 60 minutes before taking omeprazole). Additionally, most sources recommend that after taking omeprazole at least 30 minutes should be allowed to elapse before eating (at least 60 minutes for immediate-release omeprazole plus sodium bicarbonate products, such as Zegerid), though some sources say that with delayed-release forms of omeprazole it is not necessary to wait before eating after taking the medication. Plasma protein binding is about 95%. Omeprazole is completely metabolized by the cytochrome P450 system, mainly in the liver. Identified metabolites are the sulfone, the sulfide and hydroxy-omeprazole, which exert no significant effect on acid secretion. About 80% of an orally given dose is excreted as metabolites in the urine and the remainder is found in the feces, primarily originating from bile secretion.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(c2nc1ccc(OC)cc1n2)Cc3ncc(c(OC)c3C)C
(2)Std. InChI: InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)
(3)Std. InChIKey: SUBDBMMJDZJVOS-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 unreported > 600mg/kg (600mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 33, Pg. 782, 1991.
man TDLo oral 4mg/kg/2W-I (4mg/kg) MUSCULOSKELETAL: JOINTS Lancet. Vol. 345, Pg. 461, 1995.
mouse LD50 intraperitoneal > 100mg/kg (100mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988.
mouse LD50 intraperitoneal > 100mg/kg (100mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988.
mouse LD50 intravenous 82800ug/kg (82.8mg/kg)   Scandinavian Journal of Gastroenterology, Supplement. Vol. 108, Pg. 53, 1985.
mouse LD50 oral > 4gm/kg (4000mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988.
mouse LD50 subcutaneous > 100mg/kg (100mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988.
rat LD50 intraperitoneal > 100mg/kg (100mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988.
rat LD50 intravenous > 50mg/kg (50mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988.
rat LD50 oral 2210mg/kg (2210mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988.
rat LD50 subcutaneous > 100mg/kg (100mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988.
women TDLo oral 800ug/kg/2D-I (.8mg/kg) LUNGS, THORAX, OR RESPIRATION: COUGH

LUNGS, THORAX, OR RESPIRATION: PLEURAL EFFUSION
Pharmacotherapy Vol. 14, Pg. 119, 1993.
women TDLo oral 4400ug/kg/11D (4.4mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
American Journal of Gastroenterology. Vol. 94, Pg. 1119, 1999.
women TDLo oral 24mg/kg/60D-I (24mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

BLOOD: NORMOCYTIC ANEMIA
Postgraduate Medical Journal. Vol. 74, Pg. 416, 1998.
women TDLo oral 30mg/kg/10W-I (30mg/kg) BLOOD: EOSINOPHILIA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS
American Journal of Medicine. Vol. 95, Pg. 248, 1993.
women TDLo oral 36400ug/kg/13 (36.4mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Journal of Clinical Gastroenterology. Vol. 25, Pg. 718, 1997.

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